Fitness-friendly holiday rentals in Lee

4.98 out of 5 average rating, 48 reviews

A modern home with a dark exterior features large windows and a welcoming entrance. The surrounding landscape includes lush greenery and well-maintained plants, complemented by a gravel pathway leading to the front door, set against a backdrop of a clear blue sky.

Home in Great Barrington

Berkshires Family Oasis with Hot Tub, Patio, Gym

All seasons family retreat in PRIME Berkshires location. Located adjacent to the famous Appalachian trail, 5 minutes from downtown Great Barrington, 2 minutes from Ski Butternut and 15 minutes from Tanglewood in Lenox. Easy access to sensational hiking, dining, lakes and museums. The home is spacious and open with 4 BR, 7 beds, a large finished basement TV & game room space and backyard patio and hot tub. A perfect spot to enjoy the spectacular beauty and unlimited activities of the Berkshires.

5 out of 5 average rating, 117 reviews

A bright living area features large windows that invite natural light. The space includes a dark sofa, a vibrant yellow armchair, and a soft, patterned area rug. A coffee table is centrally placed, accompanied by a small side table with a decorative lamp.

Home in Taghkanic

Sunbeam Lodge: Pool+Sauna, 50 Acres, ‘70s Oasis

Our peaceful, skylit, 3-bed 2-bath lodge is a totally private woodland paradise on a quiet country lane. Part secluded retreat, part rustic resort, part '70s-style cottage, it's only 2 hours from NYC & 20 minutes from Hudson. Unwind in 50 acres of untouched forest & grounds, a seasonal saltwater pool & cabana bar, a Finnish sauna & 7-person hot tub (open year-round), an open chef's kitchen & living room, & a sunny deck overlooking endless natural splendor. See more @sunbeamlodge on Instagram.

4.99 out of 5 average rating, 342 reviews

A bright and inviting living area features large windows that offer views of the surrounding greenery. A comfortable sofa and chairs surround a coffee table, while a desk with a chair is positioned near the window for a productive workspace.

Cabin in Ghent

Cozy chalet w/ deck, fire pit, by Hudson & hiking

Cozy 3-bedroom (5-beds), 2-bathroom home on 4 private acres in charming Ghent, NY. Recently renovated, Arch Bridge Chalet offers modern clean comfort with an open floor plan, luxury bathrooms, high-end appliances and cookware, a wood-burning fireplace, outdoor deck, and fire pits. Surrounded by trees, trails, and streams, yet close to Hudson Valley farms, breweries, Berkshires skiing, and the vibrant town of Hudson. Perfect for hiking, biking, kayaking, skiing, and year-round getaways.

4.97 out of 5 average rating, 150 reviews

A serene view of a winding driveway surrounded by vibrant perennial gardens. Colorful flowers grow abundantly along the path, leading to a scenic landscape of rolling hills and distant mountains under a partly cloudy sky.

Home in Pittsfield

Hidden Oasis in the Mountains by Evergreen Home

Evergreen Home Vacation Rentals invites you to this hidden oasis in the heart of the Berkshires. This attractive 5-bedroom home features a large, fully-outfitted kitchen, Tuft & Needle mattresses, and stunning mountain views. Relax in the hot tub, enjoy the perennial gardens, or gather on the stone patio by the fire pit. Just 7 minutes to Bousquet Mountain and minutes from Lenox and Tanglewood, this is the perfect retreat for family and friends. Experience luxury and comfort—book today!

4.92 out of 5 average rating, 52 reviews

The resort area showcases a multi-story building, surrounded by green grass and landscaping. A small pond reflects the structure, while rocks line the water's edge. Trees provide additional greenery, creating a serene outdoor setting.

Hotel room in Lee

Great Place |2 BD|Kitchen| Pool 

After a day of mountain adventures , our Resort in the Berkshires is the perfect New England-y place to unwind and kick off those hiking boots. Take the whole family for a relaxing indoor swim, enjoy a flick at our onsite movie theater, and end your evening with a toast at the Beartree Bar. • Pools, Gym, Movie Theater and mini golf  • Accommodate up to 6 people  • One guest in the party, must be at least 21 y/o or older.    * U$10 PER NIGHT OF RESORT FEE(WAIVED).  **Additional charge 

4.95 out of 5 average rating, 62 reviews

Apartment in Sandisfield

Sweet Dreams Retreat

Romantic weekend getaway, featuring fireplaces, hot tub, swimmingpool, and outdoor decks . The Berkshire's, a popular vacation location. This is the perfect spot to unwind and recharge. Sweet Dreams Retreat is kept spotlessly clean and generiously stocked with everything you might need, including a full kitchen, washer and dryer, luggage racks and much more. Enjoy hiking, skiing, and a great selection of resturaunts and unique shops and more.

4.83 out of 5 average rating, 288 reviews

A charming country home is presented with a welcoming red front door. A pergola covers the entryway, surrounded by well-maintained landscaping that includes shrubs and a stone path. The exterior features light yellow siding, providing a warm, inviting appearance.

Home in Hudson

Bright, Airy Home in Hudson w/ TONS of Character!

Welcome to 514 Route 66! Conveniently located 5 min from historic Warren St, this bright and stylish country home is just minutes from downtown Hudson, where you can enjoy fine-dining restaurants, hip cocktail bars, art galleries, antique shopping, and more. Or, just relax, stay home, and sip coffee or wine in the sun-drenched living area, beneath the vaulted ceiling. A perfect mix of town and country, for a perfect upstate weekend.

5 out of 5 average rating, 18 reviews

An inviting kitchen features a central island with barstools and warm wood accents. Large windows allow natural light to fill the space, highlighting the modern appliances and tasteful decor. A dining area with additional seating is visible in the background, promoting a sense of openness.

Home in Lenox

Spacious Lenox Farmhouse | Retreat Near Tanglewood

Welcome to Green Garden! This charming 3 bedroom, 2.5 bathroom New England farmhouse is your new favorite retreat in the Berkshires. After a day of exploring, kick back by the glow of the fire pit or relax inside. Minutes from Tanglewood and downtown Lenox, you’ll enjoy farmer’s markets, great dining, and peaceful star-filled nights. The house is kid-friendly with a Pack ’n Play, Tripp Trapp high chair, and Inglesina Fast Table.

5 out of 5 average rating, 11 reviews

Townhouse in Hancock

Jiminy Peak Slopeside Getaway • Ski & Adventure

Jiminy Peak Slopeside Getaway • Ski & Adventure ★☆ ABOUT THIS SPACE ☆★ Welcome to Jiminy Peak Slopeside Getaway, your all-season mountain retreat. Enjoy scenic views and a true ski-in/ski-out experience—just a 3-minute walk to the chair lift at Jiminy Peak. This 2-bedroom, 2-bath home sleeps up to 7 guests and offers private parking, a porch, and a deck, plus access to a heated pool, indoor/outdoor hot tub, and clubhouse.

5 out of 5 average rating, 6 reviews

Home in Sheffield

All new mountain retreat near Great Barrington.

Kick back and relax in this calm, stylish space. Amazing restaurants, hiking and biking trails, fishing, and ski mountains just minutes away. Fully remodeled top to bottom with modern Scandinavian design and top of the line finishings. 5 min from Catamount, 10 min from Great Barrington, 15 min from Butternut, 25 min from Lime Rock. Great for families and pet friendly. Full gym, game room, and scenic privacy.

4.88 out of 5 average rating, 120 reviews

A charming cottage is illuminated from within, showcasing a welcoming porch with steps leading down to a spacious grassy yard. The exterior features light blue siding and a deck equipped with a grill, set against a backdrop of trees and a fenced yard.

Home in Stockbridge

Rabbit Run in the heart of Stockbridge Village

Old meets new in this lovely cottage, a short walk from the Red Lion Inn. Lots of light, comfortable, traditional furniture, beautiful, fenced-in backyard with mountain views. Kitchen updated with Smeg refrigerator, gas stove, granite counters, hardwood floors throughout. Hiking trails, park, and tennis courts within a 5-minute walk. Lake rights to Stockbridge Bowl, Weber grill, and Solo firepit.

5 out of 5 average rating, 44 reviews

Home in Monterey

Berkshires Retreat | Hiking & Swim | Fenced Yard

📍15 min to Great Barrington 📍5 min to the Appalachian Trail 📍10 min to two lakes for swimming 📍Perfect for multi-family vacations, friend getaways, and two-family trips 📍Newly renovated chef's kitchen with 48" induction range 📍Fully fenced backyard — safe for kids & dogs 📍Fire pit with wood provided 📍4 living areas + kids' hangout room 📍Games, Peloton & more 📍6-car private driveway

Popular amenities for Lee fitness-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Fitness-Friendly apartment accommodation

5 out of 5 average rating, 78 reviews

A charming entrance is framed by blooming pink shrubs and lush greenery, standing in front of a dark-colored home. The wooden fence complements the natural setting, with a soft pathway leading to the welcoming door. Sunlight filters through the trees, enhancing the peaceful ambiance.

Apartment in Lenox

Peaceful 2 BR apartment minutes from Tanglewood

5 out of 5 average rating, 4 reviews

Apartment in Wilmington

Luxury 2 Bedroom 202B

4.84 out of 5 average rating, 44 reviews

An outdoor pool area is surrounded by several lounge chairs and umbrellas, offering a view of vibrant autumn foliage on the hills. The pool is partially covered, and a building is visible in the background, enhancing the resort-like atmosphere.

Apartment in Hancock

Mountainside Condo Ski on/off

An outdoor pool is featured at the resort, surrounded by lounge chairs and umbrellas for shade. Views of the well-maintained grounds and pool area are available, with trees and hills in the background. Nearby buildings provide accommodations for guests.

Apartment in Lee

4.92 out of 5 average rating, 25 reviews

Dream Vacation

4.96 out of 5 average rating, 54 reviews

A view from the condo showcases snow-covered slopes leading up to the mountain, with ski lifts operating in the distance. The landscape is framed by the rustic stone chimney of the adjacent building, creating a serene winter scene.

Apartment in Hancock

Ski-InSki-Out Loft Lift&MT.Views

A bright bedroom features a spacious bed covered in a vibrant red comforter. Two large windows allow natural light to fill the room, complemented by neutral walls and dark curtains. A small bedside table is positioned next to the bed, adding to the cozy atmosphere.

Apartment in Albany

4.85 out of 5 average rating, 39 reviews

Limited Time Listing

Apartment in Williamstown

5 out of 5 average rating, 6 reviews

Northern Berkshire Retreat

4.73 out of 5 average rating, 11 reviews

Apartment in Schenectady

It’s Good To Be Home

Fitness-friendly condo rentals

A spacious living area features an arrangement of dark leather seating and a wooden dining table. Natural light streams through sliding glass doors that open to a balcony. A stone fireplace adds character, while decorative plants and artwork enhance the inviting ambiance.

4.94 out of 5 average rating, 71 reviews

Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base

A comfortable living area is presented with a plaid chair and a sofa, complemented by a coffee table. Natural light fills the space through a large window with elegant drapery. A flat-screen television is positioned nearby, enhancing the relaxation setting.

4.86 out of 5 average rating, 37 reviews

Jiminy Peak Apartment

The exterior of a large, two-story building is showcased against a snowy backdrop, with tall trees partially visible in the foreground. The building features arched entryways and multiple windows, while the sloped ski hill rises in the background, indicating proximity to winter sports.

4.61 out of 5 average rating, 163 reviews

Jiminy Peak Country Inn 1 Bedroom Suite

An inviting indoor pool area is surrounded by large windows that provide a view of the outdoors. Lounge chairs line the poolside, and natural light fills the space, highlighting the tiled flooring and gently rippling water.

5 out of 5 average rating, 4 reviews

Vacation Village in the Berkshires-1 BD

A lush green lawn frames a serene pond, reflecting the surrounding landscape. The two-story condo units are visible in the background, showcasing a harmonious blend with the natural setting. Towering trees provide a calming backdrop, enhancing the peaceful atmosphere of the area.

Condo in Lenox

4.7 out of 5 average rating, 10 reviews

Peaceful 1BR Condo with Pond View

A living area features a beige sofa with cushions, positioned beside a dark wood coffee table. Natural light enters through a large window with tan drapes, offering a view of grassy landscaping. A simple lamp stands next to the sofa, enhancing the cozy ambiance.

4.92 out of 5 average rating, 83 reviews

Jiminy Peak Country Inn - ski in/out condo MT view

Condo in Williamstown

Vacation Village in Berkshires 12/28/25-1/4/26

A cozy living area features a comfortable sofa grouped with an armchair and a coffee table. A large window allows natural light to illuminate the space, while curtains frame the view. A television is positioned nearby, enhancing the room's functionality.

4.73 out of 5 average rating, 15 reviews

Ski-in/Ski-Out on Jiminy Peak

Fitness-Friendly Holiday House

4.93 out of 5 average rating, 14 reviews

Home in Rhinebeck

Rhinebeck Chalet: Modern Stylish Retreat

4.77 out of 5 average rating, 70 reviews

A spacious living area showcases a blue sectional sofa with decorative pillows, paired with an orange armchair. A central coffee table holds magazines and snacks, while large windows invite natural light. A brick fireplace and an open steel staircase add character to the room.

Home in Otis

Serene Berkshires Home On 5+ Acres, Rustic & Chic

4.96 out of 5 average rating, 55 reviews

The open living area showcases a modern curved sectional sofa in dark leather, adorned with cream and patterned pillows. A sleek chandelier hangs from the high ceiling, complemented by a wall-mounted TV and a wooden fireplace. Large sliding doors lead to the outdoor patio.

Home in Hancock

Corey Road Condo | @ Jiminy Peak • Pool • Hot Tub

4.95 out of 5 average rating, 141 reviews

The exterior of the home features a well-maintained brick facade and a welcoming front entrance. A paved pathway leads to the door, flanked by vibrant flowering shrubs and manicured green lawns. Large windows provide natural light to the interior, enhancing the inviting appearance.

Home in Albany

Boho-Chic Cape Conveniently Located

4.95 out of 5 average rating, 91 reviews

A serene riverside scene features a seated statue surrounded by natural elements. Colorful fallen leaves blanket the ground, and trees provide a lush backdrop. A gentle stream flows nearby, enhancing the peaceful ambiance of the setting.

Home in Sandisfield

Lux on the River near Tanglewood w/220v EV charge

4.57 out of 5 average rating, 7 reviews

A modern lakefront home is presented at dusk, showcasing large glass windows and a spacious deck. Soft lighting from the interior adds warmth, highlighting the contemporary architecture. The surrounding lush greenery and open lawn create a serene environment, with a vibrant sunset visible in the background.

Home in Hillsdale

Hillsdale Lakeside | Lake Access, Balcony & BBQ

4.99 out of 5 average rating, 90 reviews

Home in Staatsburg

The Daydream: Hudson River Views, 4 bedrooms & Gym